Synthesis of peptides based on y-Butyrolactone scaffolds / Siti Aisyah Aliasak

• Main Author: Aliasak, Siti Aisyah
• Format: Thesis
• Language: English
• Published: 2016
• Online Access: https://ir.uitm.edu.my/id/eprint/37532/1/37532.pdf

As part of a research endeavor in investigating the synthetic utility of enantiopure azido trimethylsiloxy cyclohexene silyl ether as potential intermediates for bioactive compounds, two novel trimethylsiloxy cyclohexene peptides were synthesized. TVBocisoleucine- cyclohexene 111 a and iVBoc-leucine-cyclohexene 111 b were synthesized via reduction amination of azide, Boc protection of amine termini, deprotection of Boc group and coupling reaction with natural amino acids (iVBoc-isoleucine and JVBoc-leucine) using peptide coupling protocol. Compound 111 b was then used as the intermediate for the synthesis of incorporation y-butyrolactone-peptide via oxidative cleavage of cyclohexene double bond to afford compound 112. This compound, in turn, was used as an intermediate to afford a novel y-butyrolactone amino ester 113. These compounds can be act as versatile intermediates for further research endeavor and results extracted from this study might be used to design remarkable synthetic methodology and enhances scientific knowledge.